Combating fungi and nematodes with diphenyl-triazolyl-methanes

The present invention relates to and has for its objects the combating of fungi and nematodes with diphenyl-triazolyl-methanes, and active compositions in the form of mixtures of such compounds with solid and liquid dispersible carrier vehicles, with other and further objects becoming apparent from a study of the within specification and accompanying examples.

It has been disclosed in German Published Specification No. 1,795,249 that certain trityl-1,2,4-triazoles, such as triphenyl-(1,2,4-triazol-1-yl)-methane (Compound A), possess a good fungicidal activity. Their action is, however, not always entirely satisfactory, especially if low amounts and low concentrations are used.

It has been found that the diphenyl-triazolyl-methanes of the general formula ##STR2## in which R is alkyl, alkylcarbonyl or optionally substituted phenylcarbonyl,

X and Y each independently is halogen, alkyl, halogenoalkyl, alkoxy, alkylthio, optionally substituted phenyl or phenoxy, nitro or cyano, and

M and n each independently is an integer from 0 to 5, and their physiologically tolerated salts, exhibit powerful fungicidal and nematicidal properties.

Surprisingly, the active compounds which can be used according to the invention exhibit a substantially greater fungicidal action than the trityl-1,2,4-triazoles known from the state of the art, such as, for example, triphenyl-(1,2,4-triazol-1-yl)-methane. Their additional nematicidal action is equally surprising. Accordingly, the compounds which can be used according to the invention represent an enrichment of the art.

It is to be understood that the use of a mixture of two or more bases (I), of two or more salts or of at least one base (I) and at least one salt is comprehended herein.

The diphenyl-triazoly-methanes of the general formula (I) are derivatives of 1,2,4-triazole in which the azole radical may be linked in the 1-position or in the 4-position.

Preferably, R represents alkyl with 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part or phenylcarbonyl which is optionally substituted by halogen (especialy fluorine, chlorine or bromine) or by alkyl with 1 or 2 carbon atoms, X and Y, which may be identical or different, each represents halogen (especially fluorine, chlorine or bromine), straight-chain or branched alkyl with 1 to 4 carbon atoms, halogenoalkyl with 1 to 4 carbon atoms and up to 5 halogen atoms (especially with 1 or 2 carbon atoms and up to 3 identical or different halogen atoms, the preferred halogens being fluorine and chlorine and the trifluoromethyl group being mentioned as an example), cyano, nitro, alkoxy with 1 or 2 carbon atoms, alkylthio with 1 or 2 carbon atoms or phenyl or phenoxy, either of which is optionally substituted by halogen (especially fluorine, chlorine or bromine) or by alkyl with 1 or 2 carbon atoms, and m and n represent 0, 1, 2 or 3 (especially 0, 1 or 2).

The following may be mentioned as individual examples of the active compounds which can be used according to the invention: 1,1-diphenyl-1-(1,2,4-triazol-1-yl)-ethane, 1,1-diphenyl-1-(1,2,4-triazol-4-yl)-ethane, 1-(4-chlorophenyl-1-(1,2,4-triazol-1-yl)-ethane, 1-(4-chlorophenyl)-1-phenyl-1-(1,2,4-triazol-4-yl)-ethane, 2-(2,4-dichlorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-ethane, 1-(4-fluorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-ethane, 1-(2-methylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-ethane, 1-(3-trifluoromethylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-ethane, 1-(4-methoxyphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-ethane, 1-(4-methylthiophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-ethane, 1-(4-biphenylyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-ethane, 1-(4-biphenylyl)-1-phenyl-1-(1,2,4-triazol-4-yl)-ethane, 1-(4-4'-chlorobiphenylyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-ethane, 1-(4-phenoxyphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-ethane, 1,1-diphenyl-1 -(1,2,4-triazol-1-yl)-propane, 1,1-diphenyl-1-(1,2,4-triazol-4-yl)-propane, 1-(4-chlorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propane, 1-(4-chlorophenyl)-1-phenyl-1-(1,2,4-triazol-4-yl)-propane, 1-(4-fluorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propane, 1-(3-methylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propane, 1-(3,4-dimethylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propane, 1-(2,5-dimethylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propane, 1,1-diphenyl-1-(1,2,4-triazol-1-yl)-butane, 1,1-diphenyl-1-(1,2,4-triazol-4-yl)-butane, 1-(4-chlorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-butane, 1-(4-chlorophenyl)-1-phenyl-1-(1,2,4-triazol-4-yl)-butane, 1-(4-fluorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-butane, 1-(3-methylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-butane, 1-(3-trifluoromethylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-butane, 1,1-diphenyl-2-methyl-1-(1,2,4-triazol-1-yl)-propane, 1,1-diphenyl-1-(1,2,4-triazol-1-yl)-pentane, 1-(2-chlorophenyl)- 1-phenyl-1-(1,2,4-triazol-1-yl)-pentane, 1-(4-fluorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-pentane, 1-(3-methylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl-pentane, 1,1-diphenyl-2-methyl- 1-(1,2,4-triazol-1-yl)-butane, 1-(4-chlorophenyl)-1-phenyl-2-methyl-1-(1,2,4-triazol-1-yl)-butane, 1-(4-fluorophenyl)-1-phenyl-2-methyl-1-(1,2,4-triazol-1-yl)-butane, 1-(2-methylphenyl)-1-phenyl-2-methyl-1-(1,2,4-triazol-1-yl)-butane, 1-(2,4-dimethylphenyl)-1-phenyl-2-methyl-1-(1,2,4-triazol-1-yl)-butane, 1,1-diphenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1,1-diphenyl-2,2-dimethyl-1-(1,2,4-triazol-4-yl)-propane, 1-(2-chlorophenyl)-2-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(2-chlorophenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-4-yl)-propane, 1-(4-chlorophenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(4-chlorophenyl)- 1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-4-yl)-propane, 1-(4-fluorophenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)propane, 1-(3-trifluoromethylphenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(2-methylphenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(3-methylphenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(4-methoxyphenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(4-ethyloxyphenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(4-methylthiophenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(4-chloro-3-methylphenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(3,4-dimethylphenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(2,4-dimethylphenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(4-phenoxyphenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)propane, 1-(4-4'-chlorophenoxyphenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-( 4-biphenylyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(4-biphenylyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-4-yl)-propane, 1-(4-4'-chlorobiphenylyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(2,4-dichlorphenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(4-nitrophenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(4-cyanophenyl)-1-phenyl-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-bis-(4-chlorophenyl)-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-bis-(4-chlorophenyl)-2,2-dimethyl-1-(1,2,4-triazol-4-yl)-propane, 1-bis-(4-methylphenyl)-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(4-chlorophenyl)-1-(4-fluorophenyl)-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(4-fluorophenyl)-1-(4-phenoxyphenyl)-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1-(4-biphenylyl)-1-(4-phenoxyphenyl)-2,2-dimethyl-1-(1,2,4-triazol-1-yl)-propane, 1,1-diphenyl-1-(1,2,4-triazol-1-yl)-propan-2-one, 1,1-diphenyl-1-(1,2,4-triazol-4-yl)-propan-2-one, 1-(4-chlorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propan-2-one, 1-(4-chlorophenyl)-1-phenyl-1-(1,2,4-triazol-4-yl)-propan-2-one, 1-(2,4-dichlorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propan-2-one, 1-(4-fluorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propan-2-one, 1-(2-methylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propan-2-one, 1-(3-trifluoromethylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propan-2-one, 1-(4-methoxyphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propan-2-one, 1-(4-methylthiophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propan-2-one, 1-(4-biphenylyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propan-2-one, 1-(4-biphenylyl)-1-phenyl-1 -(1,2,4-triazol-4-yl)-propan-2-one, 1-(4-4'-chlorobiphenylyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propan-2-one, 1-(4-phenoxyphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-propan-2-one, 1,1-diphenyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1,1-diphenyl-1-(1,2,4-triazol-4-yl)-butan-2-one, 1-(4-chlorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(4-chlorophenyl)-1-phenyl-1-(1,2,4-triazol-4-yl)-butan-2-one, 1-(4-fluorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(3-methylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(3,4-dimethylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(2,5-dimethylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1,1-diphenyl-1-(1,2,4-triazol-1-yl)-pentan-2-one, 1,1-diphenyl-1-(1,2,4-triazol-4-yl)-pentan-2-one, 1-(4-chlorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-pentan-2-one, 1-(4-chlorophenyl)-1-phenyl-1-(1,2,4-triazol-4-yl)pentan-2-one, 1-(4-fluorophenyl)-1-(1,2,4-triazol-1-yl)-pentan-2-one, 1-(3-methylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-pentan-2-one, 1-(3-trifluoromethylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-pentan-2-one, 1,1-diphenyl-3-methyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1,1-diphenyl-1-(1,2,4-triazol-1-yl)-hexan-2-one, 1-(2-chlorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-hexan-2-one, 1-(4-fluorophenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-hexan-2-one, 1-(3-methylphenyl)-1-phenyl-1-(1,2,4-triazol-1-yl)-hexan-2-one, 1,1-diphenyl-3-methyl-1-(1,2,4-triazol-1-yl)-pentan-2-one, 1-(4-chlorophenyl)-1-phenyl-3-methyl-1-(1,2,4-triazol-1-yl)-pentan-2-one, 1-(4-fluorophenyl)-1-phenyl-3-methyl-1-(1,2,4-triazol-1yl)-pentan-2-one, 1-(2-methylphenyl)-1-phenyl-3-methyl-1-(1,2,4-triazol-1-yl)-pentan-2-one, 1-(2,4-dimethylphenyl)-1-phenyl-3 -methyl-1-(1,2,4-triazol-1-yl)-pentan-2-one, 1,1-diphenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1,1-diphenyl-3,3-dimethyl-1-(1,2,4-triazol-4-yl)-butan-2-one, 1-(2-chlorophenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(2-chlorophenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-4-yl)-butan-2-one, 1-(4-chlorophenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(4-chlorophenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-4-yl)-butan-2-one, 1-(4-fluorophenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one, 1-(3-trifluoromethylphenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(2-methylphenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(3-methylphenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(4-methoxyphenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(4-ethoxyphenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(4-methylthiophenyl-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(4-chloro-3-methylphenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(3,4-dimethylphenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(2,4-dimethylphenyl)1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(4-phenoxyphenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(4-4'-chlorophenoxyphenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(4-biphenylyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(4-biphenylyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-4-yl)-butan-2-one, 1-(4-4'-chlorobiphenylyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(2,4-dichlorophenyl)-1-phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(nitrophenyl)-1 -phenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(4-cyanophenyl-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-bis-(4-chlorophenyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-bis-(4-chlorophenyl)-3,3-dimethyl-1-(1,2,4-triazol-4-yl)-butan-2-one, 1-bis-(4-methylphenyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(4-chlorophenyl)-1-(4-fluorophenyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(4-fluorophenyl)-1-(4-phenoxyphenyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 1-(4-biphenylyl)-1-(4-phenoxyphenyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, benzoyl-diphenyl-1,2,4-triazol-1-yl-methane, benzoyl-diphenyl-1,2,4-triazol-4-yl-methane, benzoyl-(4-chlorophenyl)-phenyl-1,2,4-triazol-1-yl-methane, benzoyl-(4-chlorophenyl)-phenyl-1,2,4-triazol-4-yl-methane, benzoyl-(4-fluorophenyl)-phenyl- 1,2,4-triazol-1-yl-methane, benzoyl-(3-trifluoromethylphenyl)-phenyl-1,2,4-triazol-1-yl-methane, benzoyl-(3-methylphenyl)-phenyl-1,2,4-triazol-1-yl-methane, benzoyl-(4-methoxyphenyl)-phenyl-1,2,4-triazol-1-yl-methane, benzoyl-(3,4-dimethylphenyl)-phenyl-1,2,4-triazol-1-yl-methane, benzoyl-(4-chloro-3-methylphenyl)-phenyl-1,2,4-triazol-1-yl-methane, benzoyl-(4-phenoxyphenyl)-phenyl-1,2,4-triazol-1-yl-methane, benzoyl-(4,4'-chlorophenoxyphenyl)-phenyl-1,2,4-triazol-1-yl-methane, benzoyl-(4-biphenylyl)-phenyl-1,2,4-triazol-1-yl-methane, benzoyl-(4-4'-chlorobiphenylyl)-phenyl-1,2,4-triazol-1-yl-methane, benzoyl-(2,4-dichlorophenylyl)-phenyl-1,2,4-triazol-1-yl-methane, benzoyl-bis-(4-chlorophenyl)-1,2,4-triazole-1yl-methane, benzoyl-bis-(4-methylphenyl)-1,2,4-triazol-1-yl-methane, benzoyl-(4-chlorophenyl)-(4-fluorophenyl)-1,2,4-triazol-1-yl-methane, benzoyl-(4-fluorophenyl)-(4-phenoxyphenyl)-1,2,4-triazol-1-yl-methane, benzoyl-(4-bisphenylyl)-(4-phenoxyphenyl)-1,2,4-triazol-1-yl-methane, (4-chlorobenzoyl)-diphenyl-1,2,4-triazol-1-yl-methane, (4-chlorobenzoyl)-diphenyl-1,2,4-triazol-4-yl-methane, (4-chlorobenzoyl-(4-chlorophenyl)-phenyl-1,2,4-triazole-1-yl-methane, (4-chlorobenzoyl)-(4-fluorophenyl)-phenyl-1,2,4-triazol-1-yl-methane, (4-chlorobenzoyl)-(3-trifluoromethylphenyl)-phenyl-1,2,4-triazol-1-yl-methane, (4-chlorobenzoyl)-(3-methylphenyl)-phenyl-1,2,4-triazol-1-yl-methane, (4-chlorobenzoyl)-(4-phenoxyphenyl)-phenyl-1,2,4-triazole-1-yl-methane, (4-chlorobenzoyl)-( 4-biphenylyl)-phenyl-1,2,4-triazol-1-yl-methane, (4-fluorobenzoyl)-diphenyl-1,2,4-triazol-1-yl-methane, (3-methylbenzoyl)-diphenyl-1,2,4-triazol-1-yl-methane, (4-fluorobenzoyl)-(4-chlorophenyl)-phenyl-1,2,4-triazol-1-yl-methane and (3-methylbenzoyl)-(4-chlorophenyl)-phenyl-1,2,4-triazol-1-yl-methane.

Some of the compounds which can be used according to the invention are known (see German Offenlegungsschrift (German Published Specification) No. 2,037,610). However, their use as fungicides and nematicides is new.

The majority of the compounds which can be used according to the invention are new; however, they can be prepared in a simple manner, in accordance with known processes. For example, they are obtained when the corresponding known diphenyl-halogeno-methanes are reacted with 1,2,4-triazole in the presence of an acid-binding agent, for example an excess of the triazole, and, if appropriate, in the presence of a polar organic solvent, for example acetonitrile, preferably in the temperature range between 20° and 100° C., and the product is isolated in accordance with customary methods. Further details relating thereto are to be found in the preparative examples given later in this text.

Suitable salts of the compounds of the formula (I) are salts wit physiologically tolerated acids, especially the hydrogen halide acids, for example hydrobromic acid and, especially, hydrochloric acid, phosphoric acid, nitric acid, monofunctional and bifunctional carboxylic acids and hydroxycarboxylic acids, such as, for example, acetic acid, maleic acid, succinic acid, fumaric acid, citric acid, salicyclic acid, sorbic acid, tartaric acid and lactic acid, and 1,5-naphthalenedisulphonic acid.

The salts of the compounds of the formula (I) can be obtained in a simple manner in accordance with customary methods of forming salts, for example by dissolving the base in ether, for example diethyl ether, and adding the acid, for example nitric acid, and can, using known methods, be isolated, for example by filtering off, and be purified if appropriate.

The active compounds according to the invention exhibit a powerful fungitoxic action and a bacteriotoxic action. They do not damage crop plants in the concentrations required for combating fungi and bacteria. For these reasons they are suitable for use as plant protection agents for combating fungi and bacteria. Fungitoxic agents are employed in plant protection for combating Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

The active compounds according to the invention have a broad spectrum of action and can be used against parasitic fungi which attack above-ground parts of plants or which attack the plants through the soil, and also against seed-borne pathogens.

They display a particularly good activity against parasitic fungi on above-ground parts of plants, such as powdery mildew fungi, for example against species of Erysiphe and species of Podosphaera, and also against species of Venturia. In addition, they exhibit a high activity against cereal diseases, such as against cereal mildew and cereal rust. An aspect to be singled out particularly is that the active compounds according to the invention not only display a protective action, but are also curatively active, that is to say when used after infection has occurred. Furthermore, the systemic action of the compounds should be pointed out. Thus, it proves possible to protect plants against fungal attack by supplying the active compound to the above-ground parts of the plant through the soil and the root or through the seeds.

As plant protection agents, the compounds according to the invention can be used for the treatment of soil, the treatment of seed and the treatment of above-ground parts of plants. Because of their low odor and their good toleration by human skin, they are not unpleasant to handle.

When used as seed dressings, the compounds according to the invention are active against seed-borne plant diseases, namely by disinfecting the surface of the seed, for example when counteracting stripe disease of barley, and also systemically when counteracting fungal pathogens in the interior of the seed, as in the case of loose smuts of wheat and of barley. In addition, seed dressing achieves a systemic protective action against fungal infections of the shoot, for example against mildew.

The active compounds are also suitable for combating animal pests, especially nematodes, which occur in agriculture and in forestry. They are active against normally sensitive and resistant species and against all or some stages of development.

The plant-parasitic nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp. and Trichodorus spp..

The active compounds according to the instant invention can be utilized, if desired, in the form of the usual formulations or compositions with conventional inert (i.e. plant compatible or herbicidally inert) pesticide diluents or extenders, i.e. diluents, carriers or extenders of the type usable in conventional pesticide formulations or compositions, e.g. conventional pesticide dispersible carrier vehicles such as gases, solutions, emulsions, wettable powders, suspensions, powders, dusting agents, foams, pastes, soluble powders, granules, aerosols, suspension-emulsion concentrates, seed-treatment powders, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances and in coating compositions, for use on seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans, fumigating coils and the like, as well as ULV cold mist and warm mist formulations.

These are prepared in known manner, for instance by extending the active compounds with conventional pesticide dispersible liquid diluent carriers and/or dispersible solid carriers optionally with the use of carrier vehicle assistants, e.g. conventional pesticide surface-active agents, including emulsifying agents and/or dispersing agents, whereby, for example, in the case where water is used as diluent, organic solvents may be added as auxiliary solvents. The following may be chiefly considered for used as conventional carrier vehicles for this purpose: aerosol propellants which are gaseous at normal temperatures and pressures, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; inert dispersible liquid diluent carriers, including inert organic solvents, such as aromatic hydrocarbons (e.g. benzene, toluene, xylene, alkyl naphthalenes, etc.), halogenated, especially chlorinated, aromatic hydrocarbons (e.g. chlorobenzenes, etc.), cycloalkanes, (e.g. cyclohexane, etc.), paraffins (e.g. petroleum or mineral oil fractions), chlorinated aliphatic hydrocarbons (e.g. methylene chloride, dichlorodifluoromethane, trichlorofluoromethane, chloroethylenes, etc.), alcohols (e.g. methanol, ethanol, propanol, butanol, glycol, etc.) as well as ethers and esters thereof (e.g. glycol monomethyl ether, etc.), amines (e.g. ethanolamine, etc.), amides (e.g. dimethyl formamide, etc.), sulfoxides (e.g. dimethyl sulfoxide, etc.), acetonitrile, ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), and/or water; as solid carriers, ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly-dispersed silicic acid, alumina and silicates; as solid carriers for granules; crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; whereas the following may be chiefly considered for use as conventional carrier vehicle assistants, e.g. surface-active agents, for this purpose: emulsifying agents, such as non-ionic and/or anionic emulsifying agents (e.g. polyethylene oxide esters of fatty acids, polyethylene oxide ethers of fatty alcohols, alkyl sulfates, alkyl sulfonates, aryl sulfonates, albumin hydrolyzates, etc., and especially alkyl arylpolyglycol ethers, magnesium stearate, sodium oleate, etc.); and/or dispersing agents, such as lignin, sulfite waste liquors, methyl cellulose, etc.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Such active compounds may be employed alone or in the form of mixtures with one another and/or with such solid and/or liquid dispersible carrier vehicles and/or with other known compatible active agents, especially plant protection agents, such as other fungicides and nematicides, or insecticides, acaricides, bactericides, rodenticides, herbicides, fertilizers, growth-regulating agents, bird repellants, plant nutrients, agents for improving soil structure, etc., if desired, or in the form of particular dosage preparations for specificf application made therefrom, such as solutions, emulsions, suspensions, powders, pastes, and granules which are thus ready for use.

As concerns commercially marketed preparations, these generally contemplate carrier composition mixtures in which the active compound is present in an amount substantially between about 0.1-95% by weight, and preferably 0.5-90% by weight, of the mixture, whereas carrier composition mixtures suitable for direct application or field application generally contemplate those in which the active compound is present in an amount substantially between about 0.0000001-100, preferentially 0.01-10%, by weight of the mixture. Thus, the present invention contemplates overall compositions which comprise mixtures of a conventional dispersibe carrier such as (1) a dispersible inert finely divided carrier solid, and/or (2) a dispersibe carrier liquid such as an inert organic solvent and/or water, preferably including a surface-active effective amount of a carrier vehicle assistant, e.g. a surface-active agent, such as an emulsifying agent and/or a dispersing agent, and an amount of the active compound which is effective for the purpose in question and which is generally between about 0.0001-95%, and preferably 0.01-95%, by weight of the mixture.

The active compounds can also be used in accordance with the well-known ultra-low-volume process with good success, i.e. by applying such compound if normally a liquid, or by applying a liquid compositon containing the same, via very effective atomizing equipment, in finely divided form, e.g. average particle diameter of from 50-100 microns, or even less, i.e. mist form, for example by airplane crop spraying techniques. Only up to at most about a few liters/hectare are needed, and often amounts only up to about 15 to 1000 g/hectare, preferably 40 to 600 g/hectare, are sufficient. In this process it is possible to use highly concentrated liquid compositions with said liquid carrier vehicles containing from about 20 to about 95% by weight of the active compound or even the 100% active substance alone, e.g. about 20-100% by weight of the active compound.

Especially when used as leaf fungicides, the active compounds concentrations in the use forms can be varied within a fairly wide range. They are, in general, from 0.1 to 0.00001 per cent by weight, preferably from 0.05 to 0.0001 per cent.

For the treatment of seed, amounts of active compound of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are in general employed.

When used as nematicides, the active compound content can be varied within wide ranges. The active compound concentration of the use forms can be from 0.0000001 to 100% by weight of active compound, preferably from 0.01 to 10% by weight.

When used against nematodes, the preparations are generally applied to an area of agriculture in amounts of 1 to 100 kg of active compound per hectare, and are then incorporated into the soil.

When relatively high concentrations are used, the compounds usable according to the invention show plant growth-regulating properties.

Furthermore, the present invention contemplates methods of selectively killing, combating or controlling pests, e.g. fungi and nematodes, which comprises applying to at least one of correspondingly (a) such fungi, (b) such nematodes, and (c) the corresponding habitat thereof, i.e. the locus to be protected, e.g. to a growing crop, to an area where a crop is to be grown or to a domestic animal, a correspondingly combative or toxic amount, i.e. a fungicidally or nematicidally effective amount, of the particular active compound of the invention alone or together with a carrier vehicle as noted above. The instant formulations or compositions are applied in the usual manner, for instance by spraying, atomizing, vaporizing, scattering, dusting, watering, squirting, sprinkling, pouring, fumigating, dry dressing, moist dressing, wet dressing, slurry dressing, encrusting, and the like.

It will be realized, of course, that the concentration of the particular active compound utilized in admixture with the carrier vehicle will depend upon the intended application. Therefore, in special cases it is possible to go above or below the aforementioned concentration ranges.

The unexpected superiority and outstanding activity of the particular new compounds of the present invention are illustrated, without limitation, by the following examples: